The biochemistry and medical significance of the flavonoids.

In recent years, the use of essential oils (EOs) derived from aromatic plants as low-risk insecticides has increased considerably owing to their popularity with organic growers and environmentally conscious consumers. EOs are easily produced by steam distillation of plant material and contain many volatile, low-molecular-weight terpenes and phenolics. The major plant families from which EOs are extracted include Myrtaceae, Lauraceae, Lamiaceae, and Asteraceae. EOs have repellent, insecticidal, and growth-reducing effects on a variety of insects. They have been used effectively to control preharvest and postharvest phytophagous insects and as insect repellents for biting flies and for home and garden insects. The compounds exert their activities on insects through neurotoxic effects involving several mechanisms, notably through GABA, octopamine synapses, and the inhibition of acetylcholinesterase. With a few exceptions, their mammalian toxicity is low and environmental persistence is short. Registration has been the main bottleneck in putting new products on the market, but more EOs have been approved for use in the United States than elsewhere owing to reduced-risk processes for these materials.

Essential oils in insect control: low-risk products in a high-stakes world.

https://chemistry.mdma.ch/hiveboard/rhodium/pdf/piper.phytochemistry.pdf

Phytochemistry of the genus Piper

Mechanism of action of insecticidal secondary metabolites of plant origin

A review of botanical phytochemicals with mosquitocidal potential.

Extracts of 22 species of Meliaceae were examined for antimalarial activity using in vitro tests with two clones of Plasmodium falciparum, one sensitive to chloroquine (W2) and one chloroquine-resistant (D6). Twelve extracts were found to have activity, including extracts of Cedrela odorata wood and Azadirachta indica leaves, which contained the limonoid gedunin. These extracts were more effective against the W2 clone than the D6 clone, suggesting there is no cross-resistance to chloroquine. Gedunin was extracted in quantity, and nine derivatives prepared for a structure-activity study, which revealed essential functionalities for activity. The study also included four other limonoids derived from related Meliaceae. Only gedunin had better activity than chloroquine against the W2 clone. This active principle could be used to standardize a popular crude drug based on traditional use of A. indica in West Africa.

Antimalarial Activity of Tropical Meliaceae Extracts and Gedunin Derivatives

Insecticidal and growth-reducing properties of extracts of 14 species of American neotropical Piperaceae were investigated by inclusion in diets of a polyphagous lepidopteran, the European corn borer,Ostrinia nubilalis. Nutritional indices suggested most extracts acted by postdigestive toxicity.Piper aduncum, P. tuberculatum, andP. decurrens were among the most active species and were subjected to bioassay-guided isolation of the active components. Dillapiol was isolated from the active fraction ofP. aduncum, piperlonguminine was isolated fromP. tuberculatum, and a novel neolignan fromP. decurrens. The results support other studies on Asian and AfricanPiper species, which suggest that lignans and isobutyl amides are the active defence compounds in this family.

Insecticidal defenses of Piperaceae from the neotropics.

An ethnobotany study in collaboration with Q'eqchi' Maya healers of Southern Belize led to a collection of 169 medicinal plant species, belonging to 67 different families. The data show the use of a majority of species from primary or secondary semi-evergreen rainforests of Southern Belize, rather than weedy species. The medicinal uses of the plants were grouped into 17 usage categories. The frequency of use for each plant and the informant consensus factor for each usage category reveals a consensus among the healers on the use of plant species as well as on the diseases treated. These results suggest a well-defined medicinal tradition.

https://bioone.org/journals/Economic-Botany/volume-59/issue-1/0013-0001(2005)059[0029:ACEOTQ]2.0.CO;2/A-Consensus-Ethnobotany-of-the-Qeqchi-Maya-of-Southern-Belize/10.1663/0013-0001(2005)059[0029:ACEOTQ]2.0.CO;2.pdf

A consensus ethnobotany of the Q’eqchi’ Maya of Southern Belize

2,3-Dihydro-2-(4'-hydroxyphenyl)-3-methyl-5(E)-propenylbenzofuran (conocarpan) (1), 2-(4'-hydroxy-3'-methoxyphenyl)-3-methyl-5(E)- propenylbenzofuran (eupomatenoid-5) (2), and 2-(4'- hydroxyphenyl)-3-methyl-5(E)-propenylbenzofuran (eupomatenoid-6) (3), three known neolignans found for the first time in a species of the Piperaceae, were isolated from Piper decurrens via insecticidal bioassay-guided fractionation, along with a small quantity of a new related compound, 2,3-dihydro-5-formyl-2-(4'-hydroxyphenyl)-3-methylbenzofuran (decurrenal) (4), and 3,7,11,15-tetramethyl-2(E)-hexadecen-1-ol (trans-phytol).

Insecticidal Neolignans from Piper decurrens

1
 The insecticidal activity of the neotropical pepper Piper tuberculatum Jacq. and its isolated piperamides was studied. Bioassays with the mosquito Aedes atropalpus L. assessed the relative toxicity of the whole extract of Piper tuberculatum and four of the piperamides, which were isolated and identified, then prepared synthetically.

2
 The results confirm that P. tuberculatum leaf extracts are as effective as black pepper seed extract and provide an alternative pepper insecticide from a more convenient source, the leaves.

3
 Experiments with piperamides showed that the tertiary and quaternary mixtures have greater-than-additive toxicity compared to single compounds or binary mixtures. One of the four amide compounds, 4,5-dihydropiperlonguminine, was the most acutely toxic in mosquito larvae bioassays.

4
 A study of piperamide levels from different P. tuberculatum populations in Costa Rica determined that they were relatively homogeneous. Piper tuberculatum from only one of the five sites had higher levels of one piperamide, 4,5-dihydropiperine, in both leaf and stem parts. One explanation for differences in the amide concentrations between populations is that one site is ecologically unique compared to the other four.

https://www.onlinelibrary.wiley.com/doi/pdf/10.1046/j.1461-9563.2002.00137.x

Luis Poveda

Papers

Antimalarial Activity of Tropical Meliaceae Extracts and Gedunin Derivatives

Insecticidal defenses of Piperaceae from the neotropics.

A consensus ethnobotany of the Q’eqchi’ Maya of Southern Belize

Insecticidal Neolignans from Piper decurrens

Insecticidal activity of Piper tuberculatum Jacq. extracts: synergistic interaction of piperamides